The invention relates to certain novel sulfonamide compounds, to compositions containing such compounds, and to methods-of-use of such compounds to control the growth of undesired vegetation.
U.S. Pat. Nos. 4,127,405 issued Nov. 28, 1978, and 4,169,719, issued Oct. 2, 1979, both patents to Levitt, disclose certain substituted heterocyclic aryl sulfonylurea compounds and provides basic information pertaining to sulfonylurea compounds.
EPO Publication No. 70,698, published Jan. 26, 1983 teaches herbicidal indole sulfonylureas represented by the general formulas shown below. ##STR1## wherein S is SO.sub.2 NHCONH-Het;
R may be H or alkyl; R' may be H, alkyl or a carboxylic acid ester. PA0 R.sub.2 may be NR.sub.6 R.sub.7 ; PA0 R.sub.6 is H or alkyl of 1-3 carbon atoms; PA0 R.sub.7 is H or alkyl of 1-3 carbon atoms or R.sub.6 and R.sub.7 taken together are --(CH.sub.2).sub.4-5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --. PA0 R.sub.2 is H, C.sub.1 -C.sub.3 alkyl, CO.sub.2 R.sub.7 or CON(CH.sub.3).sub.2 ; PA0 R.sub.3 is H or CH.sub.3 ; PA0 R.sub.4 is H or CH.sub.3 ; PA0 R.sub.5 is H, CH.sub.3, CH.sub.2 CH.sub.3, F, Cl, Br, OCH.sub.3, OCF.sub.2 H, SCH.sub.3, SCF.sub.2 H or CF.sub.3 ; PA0 R.sub.6 is H, CH.sub.3, CH.sub.2 CH.sub.3, F, Cl, Br, OCH.sub.3, OCF.sub.2 H, SCH.sub.3, SCF.sub.2 H or CF.sub.3 ; PA0 R.sub.7 is CH.sub.3 or CH.sub.2 CH.sub.3 ; PA0 A is ##STR7## X is Cl, Br, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, OCF.sub.2 H or CF.sub.3 ; PA0 Y is H, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkyl substituted with 1-3 atoms of (a) F, (b) Cl or (c) Br, CH.sub.2 OCH.sub.3, CH.sub.2 OC.sub.2 H.sub.5, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, OCH.sub.2 CH.sub.2 OCH.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CH.sub.2 Cl, OCH.sub.2 CH.sub.2 Br, OCH.sub.2 CF.sub.3, CH(OCH.sub.3).sub.2, CH(OC.sub.2 H.sub.5).sub.2, ##STR8## or OCF.sub.2 H; Z is CH or N; PA0 X.sub.1 is O or CH.sub.2 ; PA0 Y.sub.1 is H, CH.sub.3, OCH.sub.3 or Cl; PA0 X.sub.2 is CH.sub.3, OCH.sub.3 or SCH.sub.3 ; PA0 Y.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ; and PA0 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA0 (1) when R.sub.3 is CH.sub.3, then R.sub.2 is H or CH.sub.3 ; PA0 (2) when R.sub.4 is CH.sub.3, then R.sub.2 is other than H; and PA0 (3) when X is Cl or Br, then Z is CH and Y is NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, CH.sub.3, OCH.sub.3 or OCF.sub.2 H. PA0 (1) Compounds of Formula I where A is A-1, A-2, A-3 or A-4, R is H and Y is NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, CH.sub.3, CH.sub.2 CH.sub.3, CF.sub.3, CH.sub.2 F, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CF.sub.3, CH(OCH.sub.3).sub.2, CH(OCH.sub.2 CH.sub.3).sub.2, ##STR9## or OCF.sub.2 H; (2) Compounds of Preferred 1 where R.sub.1 is H or CH.sub.3, R.sub.2 is H or CH.sub.3, R.sub.5 is H, CH.sub.3, OCH.sub.3, SCH.sub.3 or Cl and R.sub.6 is H, CH.sub.3, OCH.sub.3, SCH.sub.3 or Cl; PA0 (3) Compounds of Preferred 2 where A is A-1, X is Cl, Br, CH.sub.3 or OCH.sub.3, Y is CH.sub.3, OCH.sub.3, CH.sub.2 OCH.sub.3, OCH.sub.2 CH.sub.3 or CH(OCH.sub.3).sub.2, and R.sub.5 and R.sub.6 are H; PA0 (4) Compounds of Preferred 3 where L is L-1; PA0 (5) Compounds of Preferred 3 where L is L-2; and PA0 (6) Compounds of Preferred 3 where L is L-3. PA0 2,3-Dihydro-N-[(4methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-1H-indo le-7-sulonamide, m.p. 165.degree.-168.degree. C. PA0 2,3-Dihydro-N-[(4-methoxy-6-methyl-pyrimidin-2-yl)aminocarbonyl]-2-methyl-1 H-indole-7-sulfonamide, m.p. 175.degree.-177.degree. C.
U.S. Pat. No. 4,369,320 teaches herbicidal quinoline sulfonylureas such as the following structure: ##STR2##
EPO Publication No. 79,683, published May 25, 1983 teaches dihydrobenzofuran and dihydrobenzothiophene sulfonylureas such as: ##STR3## U.S. Pat. No. 4,369,058 teaches herbicidal benzenesulfonylureas of the general formula: ##STR4## wherein R.sub.1 may be H;
The compounds of the present application are not disclosed in the above publications or issued patents.